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A Synthesis of Taxanes by Lactam-sulfoxide Ring Contraction and Intramolecular Pinacol Coupling
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1999
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Combinatorial ChemistryBioorganic ChemistryEngineeringMolecular BiologyOrganic ChemistryChemistryHeterocycle ChemistryBiosynthesisStereoselective SynthesisBiochemistryTaxane Ring SystemNatural Product SynthesisEnantioselective SynthesisHeterocyclicNatural SciencesLactam-sulfoxide Ring ContractionOxime 10Ab-ring Moiety 3Intramolecular Pinacol CouplingSynthetic Chemistry
A synthesis of the taxane ring system is described. The A-ring moiety 5, containing the carbons for construction of the B-ring, was prepared from Wieland-Miescher ketone via Beckmann fragmentation of the oxime 10. The B-ring was formed by means of 12-membered lactam-sulfoxide ring contraction. The formation of the C-ring was carried out by aldol condensation of the resulting AB-ring moiety 3 followed by intramolecular pinacol coupling to give the tricyclic diol 23.